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- W2100046258 abstract "A series of substituted chlorinated chalcones namely, 3-(2,4-dichlorophenyl)-1-(4′-X-phenyl)-2-propen-1-one, have been synthesized, X being H, NH2, OMe, Me, F, Cl, CO2Et, CN, and NO2. Dual substituent parameter (DSP) models of 13C NMR chemical shift (CS) have revealed that π-polarization concept could be utilized to explain the reverse field effect at CO, the enhanced substituent field effect at CO, C-2, and C-5, and the decreased sensitivity of substituent field effect at C-6. Chlorine atoms dipole direction at the benzylidene ring either enhances or reduces substituent effect depending on how they couple with the substituent dipole at the probe site. The correlation of 13C NMR CS of C-2, C-5, and C-6 with σ and σ indicates that chlorine atoms in the benzylidine ring deplete the ring from charges. Both MSP of Hammett and DSP of Taft 13C NMR CS models give similar trends of substituent effects at C-2, C-5, and C-6. However, the former fail to give a significant correlation for CO and C-6 13C NMR CS. MSP of σq and DSP of Taft and Reynolds models significantly correlated 13C NMR CS of Cβ. MSP of σq fails to correlate C-1′ 13C NMR CS. Investigation of 13C NMR CS of non-chlorinated chalcones series: 3-phenyl-1-(4′-X-phenyl)-2-propen-1-one has revealed similar trends of substituent effects as in the chlorinated chalcones series for C-1′, CO, Cα, and Cβ. In contrast, the substituent effect of the non-chlorinated chalcone series at C-2, C-5, and C-6 did not correlate with any substituent constant. Copyright © 2010 John Wiley & Sons, Ltd." @default.
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- W2100046258 date "2011-01-20" @default.
- W2100046258 modified "2023-09-27" @default.
- W2100046258 title "Substituent effect investigation of 3-(2, 4-dichlorophenyl)-1-(4′-X-phenyl)-2-propen-1-one. Part 1. Correlation analysis of 13C NMR chemical shifts" @default.
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- W2100046258 doi "https://doi.org/10.1002/poc.1718" @default.
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